Nile S. Abularrage
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View article: Mammalian Esterase Activity: Implications for Peptide Prodrugs
Mammalian Esterase Activity: Implications for Peptide Prodrugs Open
As a traceless, bioreversible modification, the esterification of carboxyl groups in peptides and proteins has the potential to increase their clinical utility. An impediment is the lack of strategies to quantify esterase-catalyzed hydroly…
View article: Taming the 1,5‐sigmatropic shift across protonated spirocyclic 4<i>H</i>‐pyrazoles
Taming the 1,5‐sigmatropic shift across protonated spirocyclic 4<i>H</i>‐pyrazoles Open
The condensation of 1,3‐diketones with hydrazine to access 4 H ‐pyrazoles is a well‐established synthetic route that travels through a 4 H ‐pyrazol‐1‐ium intermediate. In the route to a 3,5‐diphenyl‐4 H ‐pyrazole containing a cyclobutane s…
View article: Cover Image
Cover Image Open
The cover image is based on the Research Article Spirocyclization enhances the Diels–Alder reactivities of geminally substituted cyclopentadienes and 4H-pyrazoles by Brian J. Levandowski, Nile S. Abularrage and Ronald T. Raines, https://on…
View article: Bioorthogonal 4<i>H</i>-pyrazole “click” reagents
Bioorthogonal 4<i>H</i>-pyrazole “click” reagents Open
4 H -Pyrazoles are emerging as useful click reagents.
View article: Spirocyclization enhances the Diels–Alder reactivities of geminally substituted cyclopentadienes and 4<i>H</i>‐pyrazoles
Spirocyclization enhances the Diels–Alder reactivities of geminally substituted cyclopentadienes and 4<i>H</i>‐pyrazoles Open
The Diels–Alder reactivity of 5‐membered dienes is tunable through spirocyclization at the saturated center. As the size of the spirocycle decreases, the Diels–Alder reactivity increases with the cyclobutane spirocycle, spiro[3.4]octa‐5,7‐…
View article: Acceleration of 1,3-Dipolar Cycloadditions by Integration of Strain and Electronic Tuning
Acceleration of 1,3-Dipolar Cycloadditions by Integration of Strain and Electronic Tuning Open
The 1,3-dipolar cycloaddition between azides and alkynes provides new means to probe and control biological processes. A major challenge is to achieve high reaction rates with stable reagents. The optimization of alkynyl reagents has relie…
View article: Differential Effects of Nitrogen Substitution in 5‐ and 6‐Membered Aromatic Motifs
Differential Effects of Nitrogen Substitution in 5‐ and 6‐Membered Aromatic Motifs Open
Invited for the cover of this issue is the group of Ronald T. Raines at the Massachusetts Institute of Technology. The image depicts the consequence of replacing carbon with nitrogen in aromatic systems, represented by Kekulé’s allegorical…
View article: Synthesis and Diels–Alder Reactivity of 4-Fluoro-4-Methyl-4H-Pyrazoles
Synthesis and Diels–Alder Reactivity of 4-Fluoro-4-Methyl-4H-Pyrazoles Open
4H-Pyrazoles are emerging scaffolds for “click” chemistry. Late-stage fluorination with Selectfluor® is found to provide a reliable route to 4-fluoro-4-methyl-4H-pyrazoles. 4-Fluoro-4-methyl-3,5-diphenyl-4H-pyrazole (MFP) manifested 7-fold…
View article: Synthesis and Diels–Alder Reactivity of 4-Fluoro-4-Methyl-4H-Pyrazoles
Synthesis and Diels–Alder Reactivity of 4-Fluoro-4-Methyl-4H-Pyrazoles Open
4H-Pyrazoles are emerging scaffolds for "click" chemistry. Late-stage fluorination with Selectfluor® is found to provide a reliable route to 4-fluoro-4-methyl-4H-pyrazoles. 4-Fluoro-4-methyl-3,5-diphenyl-4H-pyrazole (MFP) manifested 7-fold…
View article: Frontispiece: A Chemical Probe for Dehydrobutyrine
Frontispiece: A Chemical Probe for Dehydrobutyrine Open
Bioorthogonal Chemistry R. A. Scheck et al. report in their Communication on page 7350 the use of a phospha-Michael reaction to label proteins and peptides modified with dehydrobutyrine or dehydroalanine.
View article: Differential Effects of Nitrogen Substitution in 5‐ and 6‐Membered Aromatic Motifs
Differential Effects of Nitrogen Substitution in 5‐ and 6‐Membered Aromatic Motifs Open
The replacement of carbon with nitrogen can affect the aromaticity of organic rings. Nucleus‐independent chemical shift (NICS) calculations at the center of the aromatic π‐systems reveal that incorporating nitrogen into 5‐membered heteroar…
View article: Hyperconjugative Antiaromaticity Activates 4<i>H</i>-Pyrazoles as Inverse-Electron-Demand Diels–Alder Dienes
Hyperconjugative Antiaromaticity Activates 4<i>H</i>-Pyrazoles as Inverse-Electron-Demand Diels–Alder Dienes Open
The Diels-Alder reactivity of 4,4-difluoro-3,5-diphenyl-4H-pyrazole was investigated experimentally and computationally with endo-bicyclo[6.1.0]non-4-yne. The computationally predicted rate enhancement from hyperconjugative antiaromaticity…